JPH08231541A - Imidazoline derivative and herbicide - Google Patents

Abstract

PURPOSE: To obtain a new compound useful as a herbicide, having sure effects in a small dose and high safety and good in selectivity of weeds from crops. CONSTITUTION: A compound of formula I [R1 and R2 are each a 1-6C alkyl or R1 and R2 together denote a 3- to a 6-membered C ring; R3 is H, a 1-6C alkyl, COr1 or SO2r2 (r1 and r2 are each a 1-6C alkyl, etc.); Z is C, CH or N; Q is a 5- to an 8-membered ring which may contain S, N, Si or P; Y is H, a 1-6C alkyl, etc.; X is a 1-6C alkyl, a 2-6C alkenyl, a halogen, a 1-6C alkyl, phenoxy, etc.; (n) is 0-3; (m) is 0-4], e.g. 2-(5-ethyl-3-tetrahydrobenzoxazol-2-yl) pyridin-2-yl)-5-isopropyl-5-methylimidazolin-4-one. The compound of formula I is obtained by reacting a compound of formula II with a compound of formula III, providing a compound of formula IV and then heating the resultant compound of formula IV in the presence of a base (e.g. NaH). The compound is effectively used in controlling weeds such as Setaria viridis Beauv., Abutilon avicennae Gaertn. or Amaranthus lividus L.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a novel imidazoline derivative and a herbicide.

[0002]

2. Description of the Related Art In cultivating agricultural and horticultural crops, many herbicides are used for controlling weeds. However, since it causes phytotoxicity to crops, remains in the environment, and contaminates the crops, there is a demand for the development of a drug that can be used safely with a lower dose and can be used safely.

[0003]

An object of the present invention is to provide a herbicide which can be synthesized industrially advantageously, has a low dose, is highly effective, has high safety, and is highly selective to crops. is there.

[0004]

The present invention has the general formula [a]

[0005]

Embedded image

[In the formula, R ₁ and R ₂ represent a C _1-6 alkyl group, or R ₁ and R ₂ together represent a 3- to 6-membered carbocycle. R ₃ is a hydrogen atom, a C _1-6 alkyl group, a tri-C _1-6 alkylsilyl group, COr ₁ (in the formula, r
₁ represents a C _1-6 alkyl group, a C _1-6 alkoxy group or an optionally substituted phenyl group. ) Or SO ₂ r ₂
(In the formula, r ₂ represents a C _1-6 alkyl group or an optionally substituted phenyl group.).

Z represents C, CH or N. Q represents a 5- to 8-membered ring which may contain 1 or 2 carbon atoms, sulfur atom, nitrogen atom, silicon atom or phosphorus atom. Y is a hydrogen atom, C _1-6 alkyl, C _3-7 cycloalkyl, C _2-6
Alkenyl, C _3-6 alkynyl, C _1-6 haloalkyl,
Optionally substituted benzyl, optionally substituted phenyl, C _1-6 alkoxy C _1-6 alkyl, C _1-6 alkylthio C _1-6 alkyl, optionally substituted phenoxy C
_1-6 alkyl, phenylthio C _1-6 alkyl, C _1-6 alkylsulfinyl C _1-6 alkyl, C _1-6 alkylsulfonyl C _1-6 alkyl, phenylsulfonyl C _1-6 alkyl, cyano C _1-6 alkyl , Halogen, nitro, amino, C _1-6 alkylamino, di C _1-6 alkylamino, acylamino, C _1-6 alkylsulfonylamino,
Formyl, cyano, carboxyl, hydroxy, optionally substituted C _1-6 alkoxycarbonyl, optionally substituted C _1-6 alkylthiocarbonyl, C _1-6 acyl C
_1-6 alkoxymoyl, C _1-6 acylimidoyl, carbamoyl, C _1-6 alkoxy, C _2-6 alkenyloxy, C _3-6 alkynyloxy, C _1-6 alkoxy C _1-6
Alkoxy, C _1-6 alkylthio C _1-6 alkoxy, C
_1-6 alkylsulfonyl C _1-6 alkoxy, C _1-6 alkoxy substituted with C _1-6 alkoxycarbonyl, C
_1-6 alkylsulfonyloxy, thiol, C _1-6 alkylthio, C _1-6 alkylsulfonyl, C _2-6 alkenylthio, C _3-6 alkynylthio, acyloxy, carbamoyloxy, thiocarbamoyloxy, optionally substituted Benzyloxy, optionally substituted phenoxy, optionally substituted phenylthio, optionally substituted phenylsulfonyloxy, optionally substituted benzoyloxy, optionally substituted phenylsulfonyl, optionally substituted heterocycleoxy Represents an optionally substituted heterocyclic thio, an optionally substituted benzoyl, oxo, ketal or imino group.

Two Y's may combine to form a saturated or unsaturated carbocycle or heterocycle. X is (halogen atom, C _1-6 alkoxy, C _1-6 alkylthio,
C _1-6 alkylsulfonyl, C _1-6 alkoxyimino)
A C _1-6 alkyl group optionally substituted by, a C _2-6 alkenyl group _optionally substituted by phenyl, a halogen atom, C
_1-6 alkoxy group, phenoxy group, C _1-6 alkylthio group, phenylthio group, cyano, nitro, amino group optionally substituted with mono or di C _1-6 alkyl, COr ₃
(In the formula, r ₃ represents an H, C _1-6 alkyl group, a C _1-6 alkoxy group or an optionally substituted phenyl group.) Or an optionally substituted phenyl group. Alternatively, two X's may form a 5- or 6-membered carbon ring. n represents an integer of 0 to 3. m represents an integer of 0 to 4] and a herbicide.

The compound of the present invention can be produced by the following method. (Production method-1)

[0010]

[Chemical 4]

General formula [b] (wherein Q, X, Y, Z,
m and n have the same meanings as described above. ) And a compound of the general formula [c] (wherein R ₁ and R ₂ have the same meanings as described above) in an organic solvent using, for example, a dehydration condensation agent such as DCC. , General formula [d] (wherein Q,
X, Y, Z, m, n, R ₁ and R ₂ have the same meanings as described above. The compound of 1) can be synthesized. The compound [d] can also be synthesized by the following method.
That is, the compound [b] is known from the literature (eg, M. Bodan).
szky's "The Practic of Pep"
sideSynthesis ”, 1984, Spin
ger-Verlag, Berlin Heidelb
method described in erg), the general formula [e]
(Wherein Q, X, Y, Z, m and n have the same meanings as described above, and L represents a leaving group such as halogen, imidazole, lower alkoxy and nitro-substituted phenoxy). In the organic solvent, the compound [c] is reacted alone or in the presence of a suitable base. Examples of the organic solvent used in the reaction for producing the above [b] and [c] to [d] or [e] and [c] to [d] include aromatic hydrocarbons such as benzene and toluene, and chloroform. , Halogenated hydrocarbons such as dichloromethane, diethyl ether, ethers such as THF, acetone, M
Ketones such as EK, esters such as ethyl acetate, DM
Aprotic polar solvents such as F and DMSO, nitriles such as acetonitrile, organic acids such as acetic acid, and water can be mentioned. The reaction temperature is preferably 0 to 150 ° C.

The compound [d] is heated to 50 ° C to the boiling point of the solvent in a solvent such as benzene or toluene in the presence of a base such as an alkali hydroxide such as NaOH or an alkali hydride such as NaH to give a compound of the general formula [A-1] (wherein Q, X, Y,
Z, m, n, R ₁ and R ₂ have the same meanings as described above. The compound of 1) can be synthesized. Compound [a-1] in an organic solvent R ₃ ′ L ′ (R ₃ ′ represents the group represented by R ₃ except H. L ′ represents halogen, alkylsulfonyloxy or arylsulfonyloxy. ) Is reacted with a compound in the presence of a base to give a compound of the general formula [a-
2] (wherein Q, X, Y, Z, m, n, R ₁ , R ₂ , R
₃ 'are as defined above. The compound of 1) can be synthesized. Here, as the solvent, general organic solvents can be used, but DMF, DMSO, DME, THF and the like are preferable, and as the base, hydroxides, hydrides, carbonates and the like of alkali metals, and organic such as triethylamine and the like. A base can be used. The reaction temperature is 0 to 150 ° C.

(Production method-2)

[0014]

Embedded image

General formula [a-3] (wherein X'and Y'are
Each has the same meaning as X and Y. Z, m, n,
R ₁ , R ₂ , R ₃ and Q have the same meanings as described above. In a method known in the literature, the compound (1) is used alone or in the coexistence of a suitable base or acid at a temperature of −78 ° C. to the boiling point of the solvent, and a suitable reaction reagent (for example, an alkylating agent or an acylation agent). Agent, halogen, etc.) for 1 to 24 hours,
Y'm or the ring substituent X'n is derivatized to give a compound represented by the general formula [a-4] (wherein Z, m, n, R ₁ , R ₂ , R ₃ ,
Q has the same meaning as described above, and X ″ and Y ″ have the same meanings as X and Y. The compound of 1) can be synthesized.
As the organic solvent used in this reaction, for example, alcohols such as methanol, benzene, aromatic hydrocarbons such as toluene, chloroform, halogenated hydrocarbons such as dichloromethane, diethyl ether, ethers such as THF, acetone, Examples thereof include ketones such as MEK, esters such as ethyl acetate, aprotic polar solvents such as DMF and DMSO, nitriles such as acetonitrile, organic acids such as acetic acid, and water.

The base used in this reaction includes alkali hydroxides such as sodium hydroxide, carbonates such as potassium carbonate, metal alcoholates such as sodium ethylate, metals such as sodium hydride and lithium aluminum hydride. Alkyl metals such as hydride and butyl lithium,
Examples thereof include metal amides such as sodium amide, and organic bases such as triethylamine. Examples of the acid include inorganic mineral acids such as hydrochloric acid and nitric acid, organic acids such as acetic acid and trifluoromethanesulfonic acid, and Lewis acids such as aluminum chloride.

(Production Method-3) The compound of the general formula [a] is
Known literatures such as I. J. Turchi, “The
Chemistry of Heterocycle
Compounds "vol 45. John Wi
ley & Sons, Inc. , 1986 can be used for the production.

[0018]

[Chemical 6]

(Method A) General formula [f] (wherein Z, Q,
X, Y, m and n have the above-mentioned meanings. ) And a dehydration condensing agent are reacted in the absence of a solvent or a suitable solvent at room temperature to the boiling point of the solvent for 1 to 24 hours. The reaction can also be carried out in the presence of a suitable base. Examples of the dehydration condensing agent used in the reaction include phosphorus pentachloride, phosphorus oxychloride, polyphosphoric acid, phosphorus pentaoxide, triphenylphosphine-carbon tetrachloride and the like.

The solvent used in the reaction is, for example,
Examples thereof include aromatic hydrocarbons such as benzene and toluene, and halogenated hydrocarbons such as dichloromethane and chloroform. Examples of the base used include organic bases such as triethylamine, DBU and pyridine.

(Method B) General formula [g] (in the formula, Z, X, n
Indicates the above meaning. ) And an α-azide ketone represented by the general formula [h] (wherein Q, Y and m have the above-mentioned meanings) in the presence of triphenylphosphine and the like according to a method known in the literature. It is produced by reacting in a suitable solvent at room temperature to the boiling point of the solvent for 1 to 24 hours. Examples of the solvent used in the reaction include aromatic hydrocarbons such as benzene and toluene.

(Method C) General formula [g] (wherein Z, X, n
Indicates the above meaning. ) And the oxime derivative represented by the general formula [i] (wherein Q, Y and m have the above-mentioned meanings) in a suitable solvent in the presence of an acid according to a method known in the literature. , From room temperature to boiling point of solvent, 1
It is produced by reacting for -24 hours. Examples of the solvent used in the reaction include aromatic hydrocarbons such as benzene and toluene, halogenated hydrocarbons such as dichloromethane and chloroform, organic acids such as acetic acid, and acid anhydrides such as acetic anhydride. Alternatively, the compound [V] may be used in an excess amount to produce it under solvent-free conditions. Further, as the acid used in this reaction, inorganic acids such as hydrochloric acid and sulfuric acid,
Organic acids such as paratoluene sulfonic acid may be mentioned.

(D method) General formula [j] (where Z, X, n
Indicates the above meaning. ) And an α-haloketone derivative represented by the general formula [k] (wherein Q, Y and m have the above-mentioned meanings) in the presence of a suitable base according to a method known in the literature. Alternatively, it is produced by reacting in a suitable solvent or in the absence of a solvent in the absence of a solvent at room temperature to the boiling point of the solvent for 1 to 24 hours. Examples of the solvent used in the reaction include aromatic hydrocarbons such as benzene and toluene, halogenated hydrocarbons such as dichloromethane and chloroform, and the like. Examples of the base used include alkali metal hydrides, carbonates of alkali metals, triethylamine, DBU, organic bases such as pyridine.

(E method) General formula [j] (wherein Z, X, n
Indicates the above meaning. ) And an α-hydroxyketone derivative represented by the general formula [p] (wherein Q, Y and m have the above-mentioned meanings) in the presence of an acid according to a method known in the literature. It is produced by reacting in a different solvent at room temperature to the boiling point of the solvent for 1 to 24 hours. As the solvent used in the reaction, for example, benzene,
Examples thereof include aromatic hydrocarbons such as toluene, halogenated hydrocarbons such as dichloromethane and chloroform, organic acids such as acetic acid, acid anhydrides such as acetic anhydride. Examples of the acid include inorganic acids such as hydrochloric acid and sulfuric acid.

The salt of the compound represented by the general formula [a] is an environmentally acceptable salt, for example, inorganic acid salts such as hydrochloride and hydrobromide, organic salts such as acetate, oxalate and formate. Examples thereof include acid salts, alkali metals, alkaline earth metals, ammonium salts and the like. These salts may be prepared by conventional methods. The structure of the compound of the present invention was determined by IR, NMR, MS and the like.

[0026]

Examples-Compounds Next, the compounds of the present invention will be described in more detail with reference to Examples. [Example 1] 2- (5-ethyl-3- (tetrahydrobenzoxazol-2-yl) pyridin-2-yl)-
Synthesis of 5-isopropyl-5-methylimidazolin-4-one (Compound No. 25)

[0027]

[Chemical 7]

2- (5-ethyl-3- (2-hydroxycyclohexylcarbamoyl) pyridin-2-yl)-
A solution of 5-isopropyl-5-methylimidazolin-4-one (1.4 g) in methylene chloride (20 ml) was stirred at room temperature at room temperature for Dess-Martin reagent (Period).
inane) (4.6 g) was added, and the mixture was stirred at the same temperature for 4 hours. The reaction solution was filtered, and the filtrate was extracted with diluted hydrochloric acid. The aqueous solution was adjusted to pH 8 and extracted with methylene chloride. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue (0.76 g) was dissolved in methylene chloride (20 ml), carbon tetrachloride (2 ml) and triphenylphosphine (1.05 g) were added, and the mixture was heated under reflux for 6 hr. After the reaction, the solvent was distilled off under reduced pressure. The obtained residue was dissolved in ethyl acetate and extracted with diluted hydrochloric acid.
The aqueous solution was adjusted to pH 8 and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (eluting solvent hexane: acetone = 3:
Purification in 1) yielded 0.15 g of the desired product.

Representative examples of the compounds of the present invention, including the above examples, are shown in Table 1 below.

[0030]

[Table 1001]

[0031]

[Table 1002]

[0032]

[Table 1003]

The compound of the present invention (compound represented by the formula [1]) exhibits high herbicidal activity under any conditions such as soil treatment and foliage treatment under upland field conditions, and can be applied to various field weeds such as Enocologsa, velvetleaf, and barnyard grass. Effective, corn, wheat,
It also contains compounds that show selectivity for crops such as soybeans and cotton. In addition, the compound of the present invention also includes a compound having a life-growth effect on useful plants such as crops, ornamental plants and fruit trees.

Further, the compound of the present invention is
It also contains compounds that have excellent herbicidal activity against weeds such as Pleurotus cornucopia, Prunus densiflora, and Firefly, and show selectivity for rice. Furthermore, the compound of the present invention is used in orchards, lawns, track ends,
It can also be applied to control weeds in vacant land. The intermediate compounds of the compound of the present invention include those having herbicidal activity.

[Herbicides] The herbicides of the present invention contain one or more compounds of the present invention as an active ingredient. When the compound of the present invention is actually applied, it can be used in a pure form without addition of other components, and can also be used in the form of general agricultural chemicals for the purpose of being used as agricultural chemicals, that is, wettable powder, granules, powders, It can also be used in the form of emulsion, water solvent, suspension, flowable, and the like. When the purpose is a solidifying agent and a carrier, soybean powder, plant powder such as wheat flour, diatomaceous earth,
Mineral fine powders such as apatite, gypsum, talc, bentonite, pyrophyllite and clay, and organic and inorganic compounds such as sodium benzoate, urea and mirabilite are used. For the purpose of liquid dosage form, kerosene, petroleum fractions such as xylene and solvent naphtha, cyclohexane, cyclohexanone, dimethylformamide, dimethyl sulfoxide, alcohol, acetone, methyl isobutyl ketone, mineral oil, vegetable oil, water, etc. To use as. If necessary, a surfactant may be added in order to obtain a uniform and stable form in these preparations.

The concentration of the active ingredient in the herbicide of the present invention varies depending on the form of the above-mentioned preparation. For example, in the wettable powder, it is 5 to 90%, preferably 10 to 85%. : 3 to 70% in emulsion, preferably 5 to 30%, 0.01 to 30% in granule,
Preferably, a concentration of 0.05% to 10% is used.

The wettable powder and emulsion thus obtained are diluted with water to a predetermined concentration to give a suspension or emulsion, and granules are sprayed or mixed as they are before or after germination of weeds. To be done. In applying the herbicide of the present invention, an appropriate amount of 0.1 g or more of the active ingredient is applied per 10 ares.

Further, the herbicide of the present invention can be used by mixing with a known fungicide, insecticide, acaricide, herbicide, plant growth regulator and the like. In particular, it is possible to reduce the dose used by mixing with a herbicide. or,
Not only can labor saving be achieved, but a higher effect can be expected due to the synergistic action of the mixed drugs. In that case, a combination with a plurality of known herbicides is also possible.

Suitable agents to be used in combination with the herbicide of the present invention include carbamate herbicides such as bench iocarb, molinate and dimepiperate, thiocarbamate herbicides, butamide, such as butachlor, pretilachlor, mefenacet, clomethoxynil, Diphenyl ether herbicides such as biphenox, triazine herbicides such as atrazine and dianazine, sulfonylurea herbicides such as chlorsulfuron and sulfometuron-methyl, phenoxyalkanecarboxylic herbicides such as MCP and MCPB, and diclohop-methyl. Phenoxyphenoxypropionic acid herbicides, fluazifop-butyl and other pyridyloxyphenoxypropionic acid herbicides, trifluralin, pendimethalin and other dinitroaniline herbicides, and lini Ron, urea-based herbicides such as diuron, benzoyl prop ethyl, benzoylamino acid herbicides such as furan prop ethyl, imidazolinone herbicides such as imazaquin, Other, piperophos, daimuron, bentazone, die Fen zone coat,
Examples include naproanilide, etobenzanide, triazophenamide, quinclorac, and cyclohexanedione-based herbicides such as cetoxidim and cresodim.
It is also possible to add vegetable oils and oil concentrates to these combinations.

[0040]

【Example】

[Herbicides] Next, some formulation examples relating to the herbicides of the present invention will be shown, but the active ingredient compounds, additives and addition ratios are not limited to these examples, and can be varied within a wide range. Parts in the formulation examples indicate parts by weight.

Example 2 Wettable powder Compound of the present invention 20 parts White carbon 20 parts Diatomaceous earth 52 parts Sodium alkylsulfate 8 parts The above components were uniformly mixed and finely pulverized to obtain a wettable powder containing 20% of the active ingredient. .

Example 3 Emulsion Compound of the present invention 20 parts Xylene 55 parts Dimethylformamide 15 parts Polyoxyethylene phenyl ether 10 parts The above components were mixed and dissolved to obtain an emulsion containing 20% of the active ingredient.

Example 4 Granules Compound of the present invention 5 parts Talc 40 parts Clay 38 parts Bentonite 10 parts Sodium alkyl sulfate 7 parts The above components are uniformly mixed and finely pulverized, and then the diameter is 0.5 to 1.
Granules having a particle size of 0 mm were obtained to obtain granules containing 5% of the active ingredient.

[0044]

Next, test examples relating to the effects of the herbicide of the present invention will be shown. The herbicidal effect was investigated according to the following criteria and expressed as a herbicidal index.

[0045] The numerical values of 1, 3, 5, 7, and 9 represent intermediate values between 0 and 2, 2, 2 and 4, 4 and 6, 6 and 8, and 8 and 10, respectively.

[0046]

[Equation 1]

Test Example 1 Stem and Leaf Spraying A 200 cm ² pot was filled with soil, and various larvae of crabgrass, chinensis, loggrass, chinensis and velvetleaf were sown on the surface layer, lightly covered with soil and grown in a greenhouse. 5 to 1 for each weed
At the time of growing to a plant height of 0 cm, an emulsion of each test compound was diluted with water and adjusted to 1000 ppm of the chemical solution, and sprayed on the foliage of the plant with a small sprayer at a rate of 100 liter / 10a (corresponding to 100 g per 10a). . The herbicidal effect of weeds was investigated after 3 weeks, and the results are shown in Table 2.

[0048]

[Table 2]

Test Example 2 Treatment of Upland Soil A plastic pot having a surface area of 250 cm ² was filled with upland soil, and seeds of Novier, Aquinoenochogusa, velvetleaf and Acacia nilotica were sown as weeds, and 0.5 seeds were applied thereon.
cm was covered with soil. Example of the next day The diluting solution of the wettable powder shown in 1 was sprayed uniformly on the soil so that the active ingredient was 25 g per 10 a, and the herbicidal effect was investigated 3 weeks after the treatment, and the results are shown in Table 3. It was

[0050]

[Table 3]

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification code Internal reference number FI technical display location // (C07D 413/10 233: 70 263: 56) (C07D 413/10 235: 02 263: 56) ) (C07D 413/14 213: 16 233: 70 263: 52) (C07D 413/14 215: 04 233: 70 263: 52) (72) Inventor Masami Furuguchi 345 Takada, Odawara, Kanagawa Japan Odawara Research Co., Ltd. In-house (72) Inventor Takashi Kawana 345 Takada, Odawara, Kanagawa Pref., Odawara Research Laboratory, Nippon Soda Co., Ltd.

Claims (2)

[Claims] 1. A compound represented by the general formula [a]: [In the formula, R ₁ and R ₂ represent a C _1-6 alkyl group, or R ₁ and R ₂ together represent a 3- to 6-membered carbon ring. R ₃ is hydrogen atom, C _1-6 alkyl group, tri C _1-6
An alkylsilyl group, COr ₁ (in the formula, r ₁ represents a C _1-6 alkyl group, a C _1-6 alkoxy group or an optionally substituted phenyl group) or SO ₂ r ₂ (in the formula, r
₂ represents a C _1-6 alkyl group or an optionally substituted phenyl group. ). Z represents C, CH or N. Q represents a 5- to 8-membered ring which may contain 1 or 2 carbon atoms, sulfur atom, nitrogen atom, silicon atom or phosphorus atom. Y is a hydrogen atom, C _1-6 alkyl, C _3-7 cycloalkyl, C
_2-6 alkenyl, C _3-6 alkynyl, C _1-6 haloalkyl, optionally substituted benzyl, optionally substituted phenyl, C _1-6 alkoxy C _1-6 alkyl, C _1-6 alkylthio C _{1- 6} alkyl, optionally substituted phenoxy C
_1-6 alkyl, phenylthio C _1-6 alkyl, C _1-6 alkylsulfinyl C _1-6 alkyl, C _1-6 alkylsulfonyl C _1-6 alkyl, phenylsulfonyl C _1-6 alkyl, cyano C _1-6 alkyl , Halogen, nitro, amino, C _1-6 alkylamino, di C _1-6 alkylamino, acylamino, C _1-6 alkylsulfonylamino,
Formyl, cyano, carboxyl, hydroxy, optionally substituted C _1-6 alkoxycarbonyl, optionally substituted C _1-6 alkylthiocarbonyl, C _1-6 acyl C
_1-6 alkoxymoyl, C _1-6 acylimidoyl, carbamoyl, C _1-6 alkoxy, C _2-6 alkenyloxy, C _3-6 alkynyloxy, C _1-6 alkoxy C _1-6
Alkoxy, C _1-6 alkylthio C _1-6 alkoxy, C
_1-6 alkylsulfonyl C _1-6 alkoxy, C _1-6 alkoxy substituted with C _1-6 alkoxycarbonyl, C
_1-6 alkylsulfonyloxy, thiol, C _1-6 alkylthio, C _1-6 alkylsulfonyl, C _2-6 alkenylthio, C _3-6 alkynylthio, acyloxy, carbamoyloxy, thiocarbamoyloxy, optionally substituted Benzyloxy, optionally substituted phenoxy, optionally substituted phenylthio, optionally substituted phenylsulfonyloxy, optionally substituted benzoyloxy, optionally substituted phenylsulfonyl, optionally substituted heterocycleoxy Represents an optionally substituted heterocyclic thio, an optionally substituted benzoyl, oxo, ketal or imino group. Two Y's may combine to form a saturated or unsaturated carbocycle or heterocycle. X
Is a C _1-6 alkyl group optionally substituted with (halogen atom, C _1-6 alkoxy, C _1-6 alkylthio, C _1-6 alkylsulfonyl, C _1-6 alkoxyimino), substituted with phenyl Optionally substituted with a C _2-6 alkenyl group, halogen atom, C _1-6 alkoxy group, phenoxy group, C _1-6 alkylthio group, phenylthio group, cyano, nitro, mono or di C _1-6 alkyl. Amino group, C
Or ₃ (In the formula, r ₃ is an H, C _1-6 alkyl group, C _1-6
It represents an alkoxy group or an optionally substituted phenyl group. ) Or an optionally substituted phenyl group. Alternatively, two X's may form a 5- or 6-membered carbon ring. n
Represents an integer of 0 to 3. m represents an integer of 0 to 4]
The compound represented by. 2. A compound represented by the general formula [a]: _{Wherein, R 1, R 2, R} 3, Z, Q, Y, X, n and m are as defined above. ] The herbicide which contains 1 type, or 2 or more types of the compound represented by these as an active ingredient.